Pivaloyl chloride → (2S-trans)-N-[(3,4-methylenedioxy)phenyl]-3-butyloxiranecarboxamide

Under ice-cooling, to 10 ml of an anhydrous tetrahydrofuran solution containing 299 mg (1.84 mmol) of (2S-trans)-3-butyl-oxiranecarboxylic acid.dicyclohexylammonium salt was added 2 ml of an anhydroustetrahydrofuran solution containing 222 mg (1.84 mmol) of pivaloyl chloride, and the resulting mixture was stirred at the same temperature for 15 minutes. Moreover, the temperature of the reaction mixture was returned to room temperature, and the mixture was stirred for 2 hours. After insoluble material in the reaction mixture was filtered off, the filtrate was added to 10 ml of an anhydrous tetrahydrofuran solution containing 252 mg (1.84 mmol) of 3,4-methylene-dioxyaniline under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. Under reduced pressure, the reaction mixture was concentrated, ethyl acetate was added to the concentrate, and the resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and then a saturated NaCl solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 484 mg (Yield: 100%) of the title compound.

1. customwas returned to room temperature
2. stirringthe mixture was stirred for 2 hours
3. filtrationAfter insoluble material in the reaction mixture was filtered off
4. additionthe filtrate was added to 10 ml of an anhydrous tetrahydrofuran solution
5. temperaturecooling
6. stirringthe resulting mixture was stirred at room temperature for 2 hours
7. concentrationUnder reduced pressure, the reaction mixture was concentrated
8. additionethyl acetate was added to the concentrate
9. washthe resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution
10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
11. customthe solvent was removed under reduced pressure

ORD record

ord-4935f8d9cb7a4b9394456e19c946b648

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163943B2